He entered military service in 1940, and after his discharge in 1944 he returned to Reno and became part owner of the Peavine Club in 1945. After operating for little more than a year, the Peavine Club closed when the building was condemned and the property was turned into a parking lot. Bailey then opened the Harlem Club on the corner of Lake Street and Commercial Row in 1946. The Harlem club was one of the few integrated clubs in Reno at that time. After their regular shows were over, many of the African American entertainers came to the Harlem Club for unscheduled jam sessions. It was common for Pearl Bailey (Bill Bailey’s cousin), Louis Armstrong, Sammy Davis Jr., and B.B. King to play at the Harlem Club until dawn.
Bailey sold the Harlem Club in 1958. It later became known as the Soul Club. He was later a co-owner of the Happy Buddha Club and the China Mint Club.
Bailey is also remembered as a civil rights advocate, president of the Reno-Sparks NAACP, and the leader of many marches and demonstrations in the civil rights battles of the 1950’s and early 1960’s.
He retired to Edgemount, South Dakota in the early 1970’s and lived the remainder of his life on the 640-acre ranch that his father had homesteaded in 1903
Nevada State Journal, 8 Feb. 1945, 28 Apr. 1953, 26 Jan. 1956, 22July 1958, 6 Oct. 1980